# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Harry W. Gibson' _publ_contact_author_address ; Department of Chemistry Virginia Polytechnic Institute and State University Blacksburg, VA, USA, 24061 ; _publ_contact_author_email hwgibson@vt.edu _publ_contact_author_fax 540-231-8517 _publ_contact_author_phone 540-231-5902 loop_ _publ_author_name _publ_author_address 'Feihe Huang' ; Department of Chemistry Virginia Polytechnic Institute and State University Blacksburg, VA, USA, 24061 ; 'Ilia A. Guzei' ; University of Wisconsin-Madison, 2124 Chemistry Department, 1101 University Ave, Madison, WI 53706 ; 'Jason W. Jones' ; Department of Chemistry Virginia Polytechnic Institute and State University Blacksburg, VA, USA, 24061 ; 'Harry W. Gibson' ; Department of Chemistry Virginia Polytechnic Institute and State University Blacksburg, VA, USA, 24061 ; _publ_section_title ; Remarkably improved complexation of a bisparaquat by formation of a pseudocryptand-based [3]pseudorotaxane ; data_gib01 _database_code_depnum_ccdc_archive 'CCDC 218876' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C102 H138 F12 N4 O34' _chemical_formula_weight 2192.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.1544(19) _cell_length_b 15.267(3) _cell_length_c 16.196(3) _cell_angle_alpha 106.345(3) _cell_angle_beta 93.511(3) _cell_angle_gamma 106.790(3) _cell_volume 2503.2(7) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used **** _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 26.46 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1158 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9493 _exptl_absorpt_correction_T_max 0.9689 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19629 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0883 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 26.46 _reflns_number_total 9769 _reflns_number_gt 7635 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1060P)^2^+26.8156P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9769 _refine_ls_number_parameters 670 _refine_ls_number_restraints 67 _refine_ls_R_factor_all 0.2162 _refine_ls_R_factor_gt 0.1854 _refine_ls_wR_factor_ref 0.4054 _refine_ls_wR_factor_gt 0.3924 _refine_ls_goodness_of_fit_ref 1.247 _refine_ls_restrained_S_all 1.243 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F -0.1467(5) 0.1224(4) 0.3639(5) 0.0532(17) Uani 1 1 d . . . F2 F -0.0655(6) 0.0265(4) 0.3993(5) 0.0542(17) Uani 1 1 d . . . F3 F -0.0869(6) 0.0193(5) 0.2686(5) 0.072(2) Uani 1 1 d . . . F4 F 0.6173(15) 0.0698(13) 0.0737(10) 0.112(3) Uani 0.520(9) 1 d PD A 1 F5 F 0.6763(14) 0.1119(11) 0.2108(10) 0.112(3) Uani 0.520(9) 1 d PD A 1 F6 F 0.6351(14) -0.0349(10) 0.1335(12) 0.112(3) Uani 0.520(9) 1 d PD A 1 F4A F 0.5972(16) -0.0201(12) 0.0665(10) 0.112(3) Uani 0.480(9) 1 d PD A 2 F5A F 0.6409(16) 0.0064(14) 0.2032(12) 0.112(3) Uani 0.480(9) 1 d PD A 2 F6A F 0.6826(14) 0.1239(10) 0.1514(12) 0.112(3) Uani 0.480(9) 1 d PD A 2 O1 O 0.5275(6) 0.3759(4) 0.4192(4) 0.0350(15) Uani 1 1 d . . . H1 H 0.4945 0.3167 0.3931 0.052 Uiso 1 1 calc R . . O2 O 0.5996(6) 0.3889(4) 0.1300(4) 0.0334(15) Uani 1 1 d . B . O3 O 0.4594(6) 0.2622(4) -0.0333(3) 0.0293(14) Uani 1 1 d D . . O4A O 0.2732(9) 0.3050(7) -0.1091(7) 0.0371(14) Uiso 0.598(9) 1 d PD B 1 C24A C 0.4529(14) 0.2433(17) -0.1242(5) 0.0371(14) Uiso 0.598(9) 1 d PD B 1 H24A H 0.4741 0.1839 -0.1511 0.044 Uiso 0.598(9) 1 calc PR B 1 H24B H 0.5122 0.2976 -0.1379 0.044 Uiso 0.598(9) 1 calc PR B 1 C25A C 0.3177(14) 0.2310(10) -0.1563(11) 0.0371(14) Uiso 0.598(9) 1 d PD B 1 H25A H 0.3101 0.2283 -0.2182 0.044 Uiso 0.598(9) 1 calc PR B 1 H25B H 0.2626 0.1686 -0.1531 0.044 Uiso 0.598(9) 1 calc PR B 1 C26A C 0.1581(11) 0.3088(13) -0.1467(10) 0.0371(14) Uiso 0.598(9) 1 d PD B 1 H26A H 0.1552 0.2905 -0.2107 0.044 Uiso 0.598(9) 1 calc PR B 1 H26B H 0.1580 0.3763 -0.1264 0.044 Uiso 0.598(9) 1 calc PR B 1 C27A C 0.0394(16) 0.2457(12) -0.1273(6) 0.0371(14) Uiso 0.598(9) 1 d PD B 1 H27A H -0.0337 0.2558 -0.1564 0.044 Uiso 0.598(9) 1 calc PR B 1 H27B H 0.0346 0.1779 -0.1552 0.044 Uiso 0.598(9) 1 calc PR B 1 O4B O 0.2103(13) 0.2273(11) -0.1269(10) 0.0371(14) Uiso 0.402(9) 1 d PD B 2 C24B C 0.424(2) 0.237(2) -0.1242(5) 0.0371(14) Uiso 0.402(9) 1 d PD B 2 H24C H 0.4014 0.1658 -0.1478 0.044 Uiso 0.402(9) 1 calc PR B 2 H24D H 0.5012 0.2640 -0.1479 0.044 Uiso 0.402(9) 1 calc PR B 2 C25B C 0.3192(16) 0.2642(19) -0.1622(16) 0.0371(14) Uiso 0.402(9) 1 d PD B 2 H25C H 0.3425 0.3351 -0.1468 0.044 Uiso 0.402(9) 1 calc PR B 2 H25D H 0.3032 0.2364 -0.2265 0.044 Uiso 0.402(9) 1 calc PR B 2 C26B C 0.1162(18) 0.2651(18) -0.1496(16) 0.0371(14) Uiso 0.402(9) 1 d PD B 2 H26C H 0.1098 0.2585 -0.2125 0.044 Uiso 0.402(9) 1 calc PR B 2 H26D H 0.1413 0.3346 -0.1166 0.044 Uiso 0.402(9) 1 calc PR B 2 C27B C -0.011(2) 0.2143(17) -0.1307(6) 0.0371(14) Uiso 0.402(9) 1 d PD B 2 H27C H -0.0808 0.2323 -0.1548 0.044 Uiso 0.402(9) 1 calc PR B 2 H27D H -0.0317 0.1433 -0.1496 0.044 Uiso 0.402(9) 1 calc PR B 2 O5 O 0.0229(7) 0.2565(6) -0.0396(4) 0.050(2) Uani 1 1 d D . . O6 O -0.0844(6) 0.3340(5) 0.1075(5) 0.0413(17) Uani 1 1 d . B . O7 O -0.0594(6) 0.3550(5) 0.4121(5) 0.0391(17) Uani 1 1 d . B . H7 H -0.0332 0.3073 0.3973 0.059 Uiso 1 1 calc R . . O8 O -0.0668(5) 0.6199(4) 0.3138(4) 0.0249(13) Uani 1 1 d . B . O9 O 0.1032(5) 0.8060(4) 0.3646(3) 0.0186(12) Uani 1 1 d . . . O10 O 0.3611(5) 0.9145(4) 0.3735(3) 0.0176(11) Uani 1 1 d . . . O11 O 0.5621(5) 0.8374(4) 0.3925(4) 0.0220(12) Uani 1 1 d . . . O12 O 0.6398(5) 0.6710(4) 0.3497(4) 0.0250(13) Uani 1 1 d . . . O13 O 0.0866(5) 0.2414(4) 0.3939(4) 0.0268(13) Uani 1 1 d . . . O14 O 0.1590(6) 0.1176(4) 0.3437(4) 0.0306(14) Uani 1 1 d . . . O15 O 0.3834(9) -0.0499(7) 0.1289(7) 0.078(3) Uani 1 1 d . . . O16 O 0.4398(9) 0.1062(6) 0.1984(5) 0.061(2) Uani 1 1 d . . . O17 O 0.4214(6) 0.1867(4) 0.3618(4) 0.0330(15) Uani 1 1 d D . . H17O H 0.455(5) 0.161(6) 0.317(3) 0.05(3) Uiso 1 1 d D . . H17P H 0.3385(10) 0.171(6) 0.358(4) 0.03(3) Uiso 1 1 d D . . N1 N 0.2841(5) 0.6674(5) 0.4307(4) 0.0172(14) Uani 1 1 d . . . N2 N 0.2547(6) 0.2316(5) 0.1238(4) 0.0210(15) Uani 1 1 d . . . C1 C 0.3038(8) 0.7617(6) 0.4983(5) 0.0252(18) Uani 1 1 d . . . H1A H 0.2781 0.8049 0.4716 0.038 Uiso 1 1 calc R . . H1B H 0.3936 0.7905 0.5239 0.038 Uiso 1 1 calc R . . H1C H 0.2527 0.7516 0.5440 0.038 Uiso 1 1 calc R . . C2 C 0.2506(6) 0.5860(6) 0.4514(5) 0.0180(16) Uani 1 1 d . . . H2 H 0.2340 0.5883 0.5087 0.022 Uiso 1 1 calc R . . C3 C 0.2398(7) 0.4990(6) 0.3918(5) 0.0183(16) Uani 1 1 d . . . H3 H 0.2163 0.4420 0.4081 0.022 Uiso 1 1 calc R . . C4 C 0.2629(7) 0.4940(6) 0.3077(5) 0.0216(10) Uani 1 1 d . . . C5 C 0.2943(7) 0.5813(6) 0.2874(6) 0.0230(18) Uani 1 1 d . . . H5 H 0.3092 0.5813 0.2303 0.028 Uiso 1 1 calc R . . C6 C 0.3033(7) 0.6657(5) 0.3496(5) 0.0218(17) Uani 1 1 d . . . H6 H 0.3233 0.7238 0.3350 0.026 Uiso 1 1 calc R . . C7 C 0.2597(7) 0.2396(5) 0.2078(5) 0.0198(17) Uani 1 1 d . . . H7A H 0.2627 0.1863 0.2262 0.024 Uiso 1 1 calc R . . C8 C 0.2607(7) 0.3227(6) 0.2685(5) 0.0183(16) Uani 1 1 d . . . H8 H 0.2643 0.3265 0.3282 0.022 Uiso 1 1 calc R . . C9 C 0.2565(7) 0.4022(6) 0.2432(5) 0.0216(10) Uani 1 1 d . . . C10 C 0.2506(7) 0.3898(6) 0.1544(5) 0.0202(17) Uani 1 1 d . . . H10 H 0.2467 0.4415 0.1337 0.024 Uiso 1 1 calc R . . C11 C 0.2502(7) 0.3051(6) 0.0961(5) 0.0200(17) Uani 1 1 d . . . H11 H 0.2467 0.2987 0.0358 0.024 Uiso 1 1 calc R . . C12 C 0.2533(8) 0.1386(6) 0.0603(6) 0.0244(18) Uani 1 1 d . . . H12A H 0.3062 0.1095 0.0882 0.029 Uiso 1 1 calc R . . H12B H 0.2911 0.1515 0.0095 0.029 Uiso 1 1 calc R . . C13 C 0.1200(7) 0.0674(5) 0.0291(5) 0.0148(15) Uani 1 1 d . . . C14 C 0.0750(8) 0.0287(6) -0.0578(6) 0.029(2) Uani 1 1 d . . . H14 H 0.1265 0.0483 -0.0981 0.035 Uiso 1 1 calc R . . C15 C 0.0421(9) 0.0375(6) 0.0878(5) 0.029(2) Uani 1 1 d . . . H15 H 0.0716 0.0637 0.1487 0.035 Uiso 1 1 calc R . . C16 C 0.5618(7) 0.4239(6) 0.3591(6) 0.028(2) Uani 1 1 d . . . C17 C 0.5701(7) 0.3747(6) 0.2751(6) 0.026(2) Uani 1 1 d . . . H17 H 0.5586 0.3076 0.2576 0.032 Uiso 1 1 calc R . . C18 C 0.5963(7) 0.4278(6) 0.2160(6) 0.0241(18) Uani 1 1 d . . . C19 C 0.6176(8) 0.5266(7) 0.2440(6) 0.032(2) Uani 1 1 d . . . H19 H 0.6347 0.5619 0.2039 0.038 Uiso 1 1 calc R . . C20 C 0.6143(7) 0.5735(6) 0.3291(6) 0.0239(18) Uani 1 1 d . . . C21 C 0.5838(7) 0.5231(6) 0.3889(5) 0.0249(19) Uani 1 1 d . . . H21 H 0.5782 0.5551 0.4474 0.030 Uiso 1 1 calc R . . C22 C 0.5890(8) 0.2894(6) 0.0986(6) 0.032(2) Uani 1 1 d . . . H22A H 0.5127 0.2500 0.1151 0.039 Uiso 1 1 calc R B . H22B H 0.6644 0.2785 0.1240 0.039 Uiso 1 1 calc R . . C23 C 0.5795(9) 0.2620(6) 0.0020(6) 0.034(2) Uani 1 1 d . B . H23A H 0.6484 0.3084 -0.0144 0.041 Uiso 1 1 calc R . . H23B H 0.5878 0.1971 -0.0214 0.041 Uiso 1 1 calc R . . C28 C -0.0925(12) 0.2067(9) -0.0189(9) 0.065(4) Uani 1 1 d . B . H28A H -0.1078 0.1364 -0.0421 0.078 Uiso 1 1 calc R . . H28B H -0.1629 0.2213 -0.0463 0.078 Uiso 1 1 calc R . . C29 C -0.0884(10) 0.2359(7) 0.0781(8) 0.049(3) Uani 1 1 d . . . H29A H -0.1645 0.1946 0.0932 0.059 Uiso 1 1 calc R B . H29B H -0.0124 0.2284 0.1065 0.059 Uiso 1 1 calc R . . C30 C -0.0769(7) 0.3795(6) 0.1940(5) 0.0216(10) Uani 1 1 d . . . C31 C -0.0710(7) 0.3365(6) 0.2581(6) 0.030(2) Uani 1 1 d . B . H31 H -0.0712 0.2717 0.2438 0.036 Uiso 1 1 calc R . . C32 C -0.0647(7) 0.3910(6) 0.3444(7) 0.031(2) Uani 1 1 d . . . C33 C -0.0669(7) 0.4861(6) 0.3678(6) 0.0230(18) Uani 1 1 d . B . H33 H -0.0657 0.5216 0.4265 0.028 Uiso 1 1 calc R . . C34 C -0.0709(7) 0.5264(6) 0.2995(6) 0.0266(19) Uani 1 1 d . . . C35 C -0.0778(8) 0.4729(6) 0.2156(6) 0.030(2) Uani 1 1 d . B . H35 H -0.0834 0.5009 0.1707 0.036 Uiso 1 1 calc R . . C36 C -0.0451(8) 0.6817(6) 0.4009(6) 0.0235(18) Uani 1 1 d . . . H36A H 0.0254 0.6743 0.4355 0.028 Uiso 1 1 calc R B . H36B H -0.1221 0.6660 0.4283 0.028 Uiso 1 1 calc R . . C37 C -0.0122(7) 0.7826(5) 0.3968(5) 0.0166(16) Uani 1 1 d . B . H37A H -0.0802 0.7880 0.3581 0.020 Uiso 1 1 calc R . . H37B H -0.0045 0.8280 0.4556 0.020 Uiso 1 1 calc R . . C38 C 0.1426(7) 0.9012(5) 0.3604(5) 0.0194(17) Uani 1 1 d . . . H38A H 0.1605 0.9476 0.4199 0.023 Uiso 1 1 calc R . . H38B H 0.0740 0.9116 0.3264 0.023 Uiso 1 1 calc R . . C39 C 0.2589(8) 0.9179(6) 0.3184(6) 0.0232(18) Uani 1 1 d . . . H39A H 0.2436 0.8677 0.2612 0.028 Uiso 1 1 calc R . . H39B H 0.2804 0.9815 0.3088 0.028 Uiso 1 1 calc R . . C40 C 0.4770(8) 0.9420(6) 0.3417(6) 0.0250(19) Uani 1 1 d . . . H40A H 0.4960 1.0090 0.3402 0.030 Uiso 1 1 calc R . . H40B H 0.4695 0.8995 0.2816 0.030 Uiso 1 1 calc R . . C41 C 0.5821(7) 0.9354(6) 0.3983(6) 0.0227(18) Uani 1 1 d . . . H41A H 0.6640 0.9619 0.3795 0.027 Uiso 1 1 calc R . . H41B H 0.5854 0.9737 0.4594 0.027 Uiso 1 1 calc R . . C42 C 0.6631(7) 0.8267(6) 0.4417(6) 0.0240(18) Uani 1 1 d . . . H42A H 0.6740 0.8667 0.5032 0.029 Uiso 1 1 calc R . . H42B H 0.7428 0.8490 0.4188 0.029 Uiso 1 1 calc R . . C43 C 0.6360(8) 0.7237(6) 0.4365(6) 0.0265(19) Uani 1 1 d . . . H43A H 0.7001 0.7172 0.4774 0.032 Uiso 1 1 calc R . . H43B H 0.5513 0.6987 0.4523 0.032 Uiso 1 1 calc R . . C45 C 0.0766(7) 0.1565(6) 0.3632(5) 0.0181(16) Uani 1 1 d . . . C46 C -0.0567(9) 0.0819(7) 0.3455(6) 0.038(2) Uani 1 1 d . . . C47 C 0.4566(10) 0.0328(8) 0.1572(7) 0.042(2) Uani 1 1 d . A . C48 C 0.5864(14) 0.0405(7) 0.1452(7) 0.069(4) Uani 1 1 d D . . C50 C 0.449(2) 0.5042(12) 0.0156(11) 0.106(8) Uani 1 1 d . . . C51 C 0.338(3) 0.525(2) 0.043(2) 0.185(14) Uani 1 1 d . . . C52 C 0.183(3) 0.5555(17) 0.0683(16) 0.132(8) Uani 1 1 d . . . C53 C 0.0564(19) 0.5145(13) 0.0236(9) 0.085(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.021(3) 0.042(3) 0.094(5) 0.012(3) 0.013(3) 0.014(3) F2 0.048(4) 0.041(4) 0.075(5) 0.028(3) 0.019(3) 0.005(3) F3 0.037(4) 0.079(5) 0.057(4) -0.024(4) -0.001(3) -0.002(3) F4 0.071(5) 0.134(8) 0.143(9) 0.071(8) 0.033(6) 0.022(5) F5 0.071(5) 0.134(8) 0.143(9) 0.071(8) 0.033(6) 0.022(5) F6 0.071(5) 0.134(8) 0.143(9) 0.071(8) 0.033(6) 0.022(5) F4A 0.071(5) 0.134(8) 0.143(9) 0.071(8) 0.033(6) 0.022(5) F5A 0.071(5) 0.134(8) 0.143(9) 0.071(8) 0.033(6) 0.022(5) F6A 0.071(5) 0.134(8) 0.143(9) 0.071(8) 0.033(6) 0.022(5) O1 0.038(4) 0.024(3) 0.032(4) 0.006(3) -0.009(3) 0.001(3) O2 0.032(3) 0.021(3) 0.044(4) 0.007(3) 0.010(3) 0.007(3) O3 0.029(3) 0.031(3) 0.024(3) 0.004(3) 0.013(3) 0.007(3) O5 0.043(4) 0.059(5) 0.031(4) -0.020(3) -0.020(3) 0.028(4) O6 0.035(4) 0.025(3) 0.056(5) -0.004(3) -0.005(3) 0.016(3) O7 0.037(4) 0.026(3) 0.068(5) 0.023(3) 0.032(3) 0.017(3) O8 0.027(3) 0.013(3) 0.030(3) 0.001(2) -0.006(2) 0.006(2) O9 0.019(3) 0.015(3) 0.025(3) 0.007(2) 0.002(2) 0.009(2) O10 0.021(3) 0.014(3) 0.017(3) 0.006(2) 0.003(2) 0.005(2) O11 0.018(3) 0.014(3) 0.031(3) 0.002(2) 0.003(2) 0.005(2) O12 0.023(3) 0.015(3) 0.037(3) 0.006(2) 0.012(3) 0.007(2) O13 0.025(3) 0.016(3) 0.041(4) 0.009(3) 0.012(3) 0.008(2) O14 0.026(3) 0.028(3) 0.047(4) 0.018(3) 0.011(3) 0.015(3) O15 0.068(6) 0.066(6) 0.079(7) 0.006(5) 0.023(5) 0.005(5) O16 0.115(7) 0.045(5) 0.043(5) 0.009(4) 0.022(5) 0.059(5) O17 0.031(4) 0.027(3) 0.035(4) 0.008(3) -0.005(3) 0.004(3) N1 0.006(3) 0.021(3) 0.023(4) 0.004(3) 0.001(2) 0.004(2) N2 0.013(3) 0.026(4) 0.024(4) 0.005(3) 0.008(3) 0.006(3) C1 0.015(4) 0.032(5) 0.026(4) 0.008(4) -0.003(3) 0.005(3) C2 0.007(3) 0.035(5) 0.016(4) 0.014(3) 0.007(3) 0.005(3) C3 0.015(4) 0.020(4) 0.026(4) 0.014(3) 0.005(3) 0.007(3) C4 0.007(2) 0.028(2) 0.027(3) 0.007(2) 0.0013(18) 0.0034(18) C5 0.021(4) 0.025(4) 0.024(4) 0.010(4) 0.004(3) 0.006(3) C6 0.022(4) 0.011(4) 0.030(5) 0.012(3) 0.002(3) -0.002(3) C7 0.019(4) 0.016(4) 0.025(4) 0.009(3) 0.004(3) 0.002(3) C8 0.020(4) 0.029(4) 0.009(4) 0.009(3) 0.005(3) 0.007(3) C9 0.007(2) 0.028(2) 0.027(3) 0.007(2) 0.0013(18) 0.0034(18) C10 0.022(4) 0.022(4) 0.021(4) 0.015(3) 0.003(3) 0.005(3) C11 0.021(4) 0.020(4) 0.013(4) 0.004(3) 0.000(3) 0.001(3) C12 0.024(4) 0.023(4) 0.029(5) 0.009(4) 0.006(4) 0.009(3) C13 0.022(4) 0.012(4) 0.014(4) 0.001(3) 0.003(3) 0.013(3) C14 0.025(4) 0.035(5) 0.028(5) 0.015(4) 0.017(4) 0.003(4) C15 0.037(5) 0.029(5) 0.011(4) 0.000(3) -0.001(3) 0.003(4) C16 0.010(4) 0.028(5) 0.037(5) 0.007(4) -0.009(3) 0.000(3) C17 0.015(4) 0.010(4) 0.048(6) -0.001(4) -0.001(4) 0.005(3) C18 0.017(4) 0.017(4) 0.033(5) 0.000(4) 0.011(3) 0.004(3) C19 0.023(5) 0.030(5) 0.046(6) 0.018(4) 0.006(4) 0.009(4) C20 0.010(4) 0.025(4) 0.030(5) 0.001(4) 0.004(3) 0.001(3) C21 0.020(4) 0.027(4) 0.021(4) -0.007(3) -0.001(3) 0.010(3) C22 0.021(4) 0.021(4) 0.051(6) 0.008(4) 0.007(4) 0.003(4) C23 0.034(5) 0.018(4) 0.048(6) 0.005(4) 0.027(4) 0.006(4) C28 0.050(7) 0.045(7) 0.083(9) -0.025(6) -0.022(6) 0.039(6) C29 0.030(5) 0.021(5) 0.078(8) -0.011(5) -0.001(5) 0.010(4) C30 0.007(2) 0.028(2) 0.027(3) 0.007(2) 0.0013(18) 0.0034(18) C31 0.015(4) 0.012(4) 0.056(6) -0.004(4) 0.010(4) 0.009(3) C32 0.009(4) 0.021(4) 0.071(7) 0.025(5) 0.013(4) 0.004(3) C33 0.008(4) 0.021(4) 0.040(5) 0.007(4) 0.008(3) 0.006(3) C34 0.012(4) 0.023(4) 0.038(5) 0.002(4) 0.002(3) 0.004(3) C35 0.020(4) 0.023(4) 0.044(6) 0.005(4) -0.006(4) 0.008(4) C36 0.017(4) 0.021(4) 0.035(5) 0.009(4) 0.006(3) 0.011(3) C37 0.015(4) 0.014(4) 0.021(4) 0.003(3) 0.004(3) 0.008(3) C38 0.025(4) 0.008(3) 0.020(4) 0.001(3) -0.010(3) 0.005(3) C39 0.031(5) 0.013(4) 0.028(5) 0.009(3) 0.003(4) 0.009(3) C40 0.032(5) 0.010(4) 0.028(5) 0.007(3) 0.017(4) -0.003(3) C41 0.016(4) 0.019(4) 0.028(5) 0.002(3) 0.008(3) 0.002(3) C42 0.008(4) 0.027(4) 0.031(5) 0.004(4) 0.005(3) 0.000(3) C43 0.021(4) 0.024(4) 0.032(5) 0.002(4) 0.003(4) 0.011(3) C45 0.024(4) 0.028(4) 0.009(4) 0.007(3) 0.011(3) 0.016(3) C46 0.036(5) 0.044(6) 0.028(5) 0.003(4) 0.001(4) 0.010(5) C47 0.043(6) 0.041(6) 0.043(6) 0.021(5) 0.002(5) 0.008(5) C48 0.081(10) 0.052(8) 0.095(11) 0.042(8) 0.021(8) 0.031(7) C50 0.138(19) 0.063(9) 0.073(11) 0.019(8) 0.037(11) -0.033(11) C51 0.13(2) 0.24(3) 0.28(4) 0.22(3) 0.06(2) 0.06(2) C52 0.17(2) 0.15(2) 0.140(19) 0.123(17) 0.057(17) 0.066(17) C53 0.147(18) 0.107(13) 0.045(9) 0.040(9) 0.019(9) 0.086(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C46 1.331(11) . ? F2 C46 1.363(12) . ? F3 C46 1.293(11) . ? F4 C48 1.382(9) . ? F5 C48 1.382(9) . ? F6 C48 1.381(9) . ? F4A C48 1.383(9) . ? F5A C48 1.383(9) . ? F6A C48 1.382(9) . ? O1 C16 1.384(11) . ? O2 C18 1.360(10) . ? O2 C22 1.427(10) . ? O3 C24A 1.411(7) . ? O3 C24B 1.411(7) . ? O3 C23 1.426(12) . ? O4A C26A 1.411(7) . ? O4A C25A 1.411(7) . ? C24A C25A 1.506(13) . ? C26A C27A 1.506(13) . ? C27A O5 1.412(7) . ? O4B C25B 1.411(7) . ? O4B C26B 1.411(7) . ? C24B C25B 1.505(13) . ? C26B C27B 1.505(13) . ? C27B O5 1.410(7) . ? O5 C28 1.406(16) . ? O6 C30 1.363(11) . ? O6 C29 1.425(11) . ? O7 C32 1.363(12) . ? O8 C34 1.367(10) . ? O8 C36 1.419(10) . ? O9 C37 1.406(9) . ? O9 C38 1.415(9) . ? O10 C40 1.415(9) . ? O10 C39 1.426(10) . ? O11 C42 1.414(10) . ? O11 C41 1.423(9) . ? O12 C20 1.369(10) . ? O12 C43 1.419(10) . ? O13 C45 1.219(9) . ? O14 C45 1.241(9) . ? O15 C47 1.226(13) . ? O16 C47 1.205(13) . ? N1 C2 1.335(10) . ? N1 C6 1.338(10) . ? N1 C1 1.490(10) . ? N2 C7 1.327(10) . ? N2 C11 1.334(10) . ? N2 C12 1.496(10) . ? C2 C3 1.372(11) . ? C3 C4 1.386(11) . ? C4 C5 1.414(11) . ? C4 C9 1.473(12) . ? C5 C6 1.366(12) . ? C7 C8 1.365(11) . ? C8 C9 1.397(11) . ? C9 C10 1.392(11) . ? C10 C11 1.369(11) . ? C12 C13 1.520(11) . ? C13 C14 1.362(12) . ? C13 C15 1.408(11) . ? C14 C15 1.359(12) 2 ? C15 C14 1.359(12) 2 ? C16 C17 1.381(13) . ? C16 C21 1.395(12) . ? C17 C18 1.411(13) . ? C18 C19 1.390(12) . ? C19 C20 1.370(13) . ? C20 C21 1.398(13) . ? C22 C23 1.490(14) . ? C28 C29 1.503(18) . ? C30 C35 1.372(12) . ? C30 C31 1.383(13) . ? C31 C32 1.397(14) . ? C32 C33 1.402(12) . ? C33 C34 1.413(13) . ? C34 C35 1.359(13) . ? C36 C37 1.498(11) . ? C38 C39 1.492(12) . ? C40 C41 1.487(12) . ? C42 C43 1.490(12) . ? C45 C46 1.542(13) . ? C47 C48 1.448(18) . ? C50 C50 1.31(4) 2_665 ? C50 C51 1.42(3) . ? C51 C52 1.96(4) . ? C52 C53 1.42(3) . ? C53 C53 1.32(4) 2_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C18 O2 C22 118.1(7) . . ? C24A O3 C24B 12.5(13) . . ? C24A O3 C23 109.1(8) . . ? C24B O3 C23 120.5(10) . . ? C26A O4A C25A 116.4(12) . . ? O3 C24A C25A 104.7(11) . . ? O4A C25A C24A 114.0(14) . . ? O4A C26A C27A 115.7(13) . . ? O5 C27A C26A 119.1(12) . . ? C25B O4B C26B 108.4(16) . . ? O3 C24B C25B 121.3(18) . . ? O4B C25B C24B 107.0(18) . . ? O4B C26B C27B 111.8(18) . . ? O5 C27B C26B 94.1(15) . . ? C28 O5 C27B 95.8(11) . . ? C28 O5 C27A 120.6(9) . . ? C27B O5 C27A 25.1(8) . . ? C30 O6 C29 120.2(8) . . ? C34 O8 C36 118.8(6) . . ? C37 O9 C38 112.8(6) . . ? C40 O10 C39 111.1(6) . . ? C42 O11 C41 111.7(6) . . ? C20 O12 C43 118.3(6) . . ? C2 N1 C6 120.5(7) . . ? C2 N1 C1 120.2(7) . . ? C6 N1 C1 119.2(7) . . ? C7 N2 C11 120.6(7) . . ? C7 N2 C12 119.2(7) . . ? C11 N2 C12 120.3(7) . . ? N1 C2 C3 121.4(7) . . ? C2 C3 C4 120.2(7) . . ? C3 C4 C5 116.8(7) . . ? C3 C4 C9 121.4(7) . . ? C5 C4 C9 121.8(7) . . ? C6 C5 C4 120.3(8) . . ? N1 C6 C5 120.8(7) . . ? N2 C7 C8 121.6(7) . . ? C7 C8 C9 120.3(7) . . ? C10 C9 C8 115.8(7) . . ? C10 C9 C4 122.8(8) . . ? C8 C9 C4 121.4(7) . . ? C11 C10 C9 121.7(7) . . ? N2 C11 C10 120.0(7) . . ? N2 C12 C13 112.2(6) . . ? C14 C13 C15 118.5(7) . . ? C14 C13 C12 119.8(7) . . ? C15 C13 C12 121.7(7) . . ? C15 C14 C13 121.2(8) 2 . ? C14 C15 C13 120.3(8) 2 . ? C17 C16 O1 121.0(8) . . ? C17 C16 C21 123.4(8) . . ? O1 C16 C21 115.6(8) . . ? C16 C17 C18 117.5(7) . . ? O2 C18 C19 115.3(8) . . ? O2 C18 C17 124.5(7) . . ? C19 C18 C17 120.2(8) . . ? C20 C19 C18 120.5(9) . . ? O12 C20 C19 115.4(8) . . ? O12 C20 C21 123.3(7) . . ? C19 C20 C21 121.3(8) . . ? C16 C21 C20 117.1(8) . . ? O2 C22 C23 107.5(8) . . ? O3 C23 C22 108.6(7) . . ? O5 C28 C29 110.0(9) . . ? O6 C29 C28 108.1(10) . . ? O6 C30 C35 115.9(8) . . ? O6 C30 C31 123.9(8) . . ? C35 C30 C31 120.2(8) . . ? C30 C31 C32 118.2(7) . . ? O7 C32 C31 122.7(8) . . ? O7 C32 C33 114.8(9) . . ? C31 C32 C33 122.5(9) . . ? C32 C33 C34 116.6(8) . . ? C35 C34 O8 116.8(8) . . ? C35 C34 C33 120.6(8) . . ? O8 C34 C33 122.6(8) . . ? C34 C35 C30 121.8(9) . . ? O8 C36 C37 106.8(7) . . ? O9 C37 C36 109.3(6) . . ? O9 C38 C39 109.8(6) . . ? O10 C39 C38 109.1(6) . . ? O10 C40 C41 110.6(7) . . ? O11 C41 C40 109.5(6) . . ? O11 C42 C43 109.8(6) . . ? O12 C43 C42 108.0(7) . . ? O13 C45 O14 130.2(8) . . ? O13 C45 C46 117.9(7) . . ? O14 C45 C46 111.9(7) . . ? F3 C46 F1 110.9(8) . . ? F3 C46 F2 103.3(9) . . ? F1 C46 F2 103.3(8) . . ? F3 C46 C45 114.6(8) . . ? F1 C46 C45 112.8(8) . . ? F2 C46 C45 111.0(8) . . ? O16 C47 O15 130.6(12) . . ? O16 C47 C48 115.6(10) . . ? O15 C47 C48 113.5(10) . . ? F6 C48 F6A 109.4(16) . . ? F6 C48 F4 101.2(8) . . ? F6A C48 F4 57.2(8) . . ? F6 C48 F5 101.2(8) . . ? F6A C48 F5 43.9(8) . . ? F4 C48 F5 101.1(8) . . ? F6 C48 F4A 53.4(9) . . ? F6A C48 F4A 101.1(8) . . ? F4 C48 F4A 55.8(7) . . ? F5 C48 F4A 131.8(16) . . ? F6 C48 F5A 47.6(9) . . ? F6A C48 F5A 101.1(8) . . ? F4 C48 F5A 137.2(16) . . ? F5 C48 F5A 66.2(8) . . ? F4A C48 F5A 101.0(8) . . ? F6 C48 C47 124.0(11) . . ? F6A C48 C47 126.3(12) . . ? F4 C48 C47 112.0(11) . . ? F5 C48 C47 114.3(12) . . ? F4A C48 C47 113.6(12) . . ? F5A C48 C47 110.4(12) . . ? C50 C50 C51 171(3) 2_665 . ? C50 C51 C52 174(2) . . ? C53 C52 C51 132(2) . . ? C53 C53 C52 172(2) 2_565 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C24B O3 C24A C25A 15(9) . . . . ? C23 O3 C24A C25A 172.1(12) . . . . ? C26A O4A C25A C24A 167.0(14) . . . . ? O3 C24A C25A O4A 49(2) . . . . ? C25A O4A C26A C27A 85.7(17) . . . . ? O4A C26A C27A O5 57(2) . . . . ? C24A O3 C24B C25B -136(12) . . . . ? C23 O3 C24B C25B -161.3(19) . . . . ? C26B O4B C25B C24B 170(2) . . . . ? O3 C24B C25B O4B -56(3) . . . . ? C25B O4B C26B C27B 168.3(19) . . . . ? O4B C26B C27B O5 72(2) . . . . ? C26B C27B O5 C28 -177.2(13) . . . . ? C26B C27B O5 C27A 11(3) . . . . ? C26A C27A O5 C28 172.8(12) . . . . ? C26A C27A O5 C27B -178(4) . . . . ? C6 N1 C2 C3 2.6(11) . . . . ? C1 N1 C2 C3 -175.8(7) . . . . ? N1 C2 C3 C4 -0.4(11) . . . . ? C2 C3 C4 C5 -1.5(11) . . . . ? C2 C3 C4 C9 177.8(7) . . . . ? C3 C4 C5 C6 1.3(11) . . . . ? C9 C4 C5 C6 -178.0(7) . . . . ? C2 N1 C6 C5 -2.8(11) . . . . ? C1 N1 C6 C5 175.6(7) . . . . ? C4 C5 C6 N1 0.8(12) . . . . ? C11 N2 C7 C8 -0.2(11) . . . . ? C12 N2 C7 C8 -179.7(7) . . . . ? N2 C7 C8 C9 0.0(12) . . . . ? C7 C8 C9 C10 0.4(11) . . . . ? C7 C8 C9 C4 -177.4(7) . . . . ? C3 C4 C9 C10 165.1(7) . . . . ? C5 C4 C9 C10 -15.7(11) . . . . ? C3 C4 C9 C8 -17.3(11) . . . . ? C5 C4 C9 C8 161.9(7) . . . . ? C8 C9 C10 C11 -0.6(11) . . . . ? C4 C9 C10 C11 177.1(7) . . . . ? C7 N2 C11 C10 0.0(11) . . . . ? C12 N2 C11 C10 179.5(7) . . . . ? C9 C10 C11 N2 0.4(12) . . . . ? C7 N2 C12 C13 86.6(9) . . . . ? C11 N2 C12 C13 -93.0(8) . . . . ? N2 C12 C13 C14 124.9(8) . . . . ? N2 C12 C13 C15 -57.2(10) . . . . ? C15 C13 C14 C15 -0.1(14) . . . 2 ? C12 C13 C14 C15 177.8(8) . . . 2 ? C14 C13 C15 C14 0.1(14) . . . 2 ? C12 C13 C15 C14 -177.8(8) . . . 2 ? O1 C16 C17 C18 175.3(7) . . . . ? C21 C16 C17 C18 -3.1(12) . . . . ? C22 O2 C18 C19 174.8(7) . . . . ? C22 O2 C18 C17 -6.8(12) . . . . ? C16 C17 C18 O2 -175.7(7) . . . . ? C16 C17 C18 C19 2.6(12) . . . . ? O2 C18 C19 C20 178.8(7) . . . . ? C17 C18 C19 C20 0.3(12) . . . . ? C43 O12 C20 C19 179.1(7) . . . . ? C43 O12 C20 C21 0.5(11) . . . . ? C18 C19 C20 O12 178.4(7) . . . . ? C18 C19 C20 C21 -2.9(12) . . . . ? C17 C16 C21 C20 0.7(12) . . . . ? O1 C16 C21 C20 -177.8(7) . . . . ? O12 C20 C21 C16 -179.1(7) . . . . ? C19 C20 C21 C16 2.4(12) . . . . ? C18 O2 C22 C23 173.3(7) . . . . ? C24A O3 C23 C22 175.7(12) . . . . ? C24B O3 C23 C22 -178.7(17) . . . . ? O2 C22 C23 O3 -70.0(8) . . . . ? C27B O5 C28 C29 179.9(13) . . . . ? C27A O5 C28 C29 -176.1(11) . . . . ? C30 O6 C29 C28 -178.3(8) . . . . ? O5 C28 C29 O6 67.5(10) . . . . ? C29 O6 C30 C35 -177.9(8) . . . . ? C29 O6 C30 C31 1.0(12) . . . . ? O6 C30 C31 C32 -179.5(7) . . . . ? C35 C30 C31 C32 -0.7(11) . . . . ? C30 C31 C32 O7 179.5(7) . . . . ? C30 C31 C32 C33 1.4(12) . . . . ? O7 C32 C33 C34 179.3(7) . . . . ? C31 C32 C33 C34 -2.4(11) . . . . ? C36 O8 C34 C35 -172.9(7) . . . . ? C36 O8 C34 C33 6.4(11) . . . . ? C32 C33 C34 C35 2.7(11) . . . . ? C32 C33 C34 O8 -176.5(7) . . . . ? O8 C34 C35 C30 177.1(7) . . . . ? C33 C34 C35 C30 -2.2(12) . . . . ? O6 C30 C35 C34 180.0(7) . . . . ? C31 C30 C35 C34 1.1(12) . . . . ? C34 O8 C36 C37 165.7(6) . . . . ? C38 O9 C37 C36 -178.7(6) . . . . ? O8 C36 C37 O9 -65.1(8) . . . . ? C37 O9 C38 C39 -174.9(6) . . . . ? C40 O10 C39 C38 -172.5(6) . . . . ? O9 C38 C39 O10 -66.5(8) . . . . ? C39 O10 C40 C41 -178.3(6) . . . . ? C42 O11 C41 C40 176.9(6) . . . . ? O10 C40 C41 O11 65.9(8) . . . . ? C41 O11 C42 C43 177.9(6) . . . . ? C20 O12 C43 C42 -178.4(7) . . . . ? O11 C42 C43 O12 67.9(8) . . . . ? O13 C45 C46 F3 130.6(9) . . . . ? O14 C45 C46 F3 -50.2(11) . . . . ? O13 C45 C46 F1 2.5(11) . . . . ? O14 C45 C46 F1 -178.3(8) . . . . ? O13 C45 C46 F2 -112.9(9) . . . . ? O14 C45 C46 F2 66.3(10) . . . . ? O16 C47 C48 F6 152.4(11) . . . . ? O15 C47 C48 F6 -22.4(15) . . . . ? O16 C47 C48 F6A -21.2(15) . . . . ? O15 C47 C48 F6A 163.9(11) . . . . ? O16 C47 C48 F4 -85.9(12) . . . . ? O15 C47 C48 F4 99.3(12) . . . . ? O16 C47 C48 F5 28.3(13) . . . . ? O15 C47 C48 F5 -146.6(11) . . . . ? O16 C47 C48 F4A -146.9(11) . . . . ? O15 C47 C48 F4A 38.3(14) . . . . ? O16 C47 C48 F5A 100.6(12) . . . . ? O15 C47 C48 F5A -74.3(13) . . . . ? C50 C50 C51 C52 33(39) 2_665 . . . ? C50 C51 C52 C53 57(26) . . . . ? C51 C52 C53 C53 -90(16) . . . 2_565 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O17 0.84 1.82 2.643(9) 166.8 . O7 H7 O13 0.84 1.89 2.675(8) 155.7 . O17 H17P O14 0.880(2) 1.902(15) 2.776(9) 172(8) . O17 H17O O16 0.880(2) 1.85(4) 2.634(10) 148(7) . _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.930 _refine_diff_density_min -1.055 _refine_diff_density_rms 0.122